JP3287660B2 - 紙仕上げ用の無塩素多官能樹脂 - Google Patents

紙仕上げ用の無塩素多官能樹脂

Info

Publication number: JP3287660B2
Authority: JP; Japan
Prior art keywords: mixture; groups; water; polyisocyanate; nco
Prior art date: 1992-08-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

JP21359093A

Other languages

English (en)

Japanese (ja)

Other versions

JPH06173196A (ja

Inventor

ユルゲン・ライナース

ハンス−ヨゼフ・ラース

ヨアヒム・ケーニヒ

ヘルムート・ライフ

ヨアヒム・プロプスト

ブルノ・ベマー

ラインハルト・ハルパープ

フリツツ・プフナー

ハロ・トロイベル

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-08-07

Filing date

1993-08-06

Publication date

2002-06-04

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25917292&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JP3287660(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1992-08-07 Priority claimed from DE19924226110 external-priority patent/DE4226110A1/de

1993-06-14 Priority claimed from DE19934319571 external-priority patent/DE4319571A1/de

1993-08-06 Application filed by Bayer AG filed Critical Bayer AG

1994-06-21 Publication of JPH06173196A publication Critical patent/JPH06173196A/ja

2002-06-04 Application granted granted Critical

2002-06-04 Publication of JP3287660B2 publication Critical patent/JP3287660B2/ja

2017-06-04 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920005989 resin Polymers 0.000 title description 16
239000011347 resin Substances 0.000 title description 16
239000005056 polyisocyanate Substances 0.000 claims description 190
229920001228 polyisocyanate Polymers 0.000 claims description 190
239000000203 mixture Substances 0.000 claims description 155
230000009257 reactivity Effects 0.000 claims description 51
238000000034 method Methods 0.000 claims description 44
125000001302 tertiary amino group Chemical group 0.000 claims description 43
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 42
239000001913 cellulose Substances 0.000 claims description 31
229920002678 cellulose Polymers 0.000 claims description 31
239000000463 material Substances 0.000 claims description 31
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 30
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 30
-1 polyethylene Polymers 0.000 claims description 19
238000004519 manufacturing process Methods 0.000 claims description 16
239000006185 dispersion Substances 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 10
238000009472 formulation Methods 0.000 claims description 3
239000004698 Polyethylene Substances 0.000 claims 1
229920000573 polyethylene Polymers 0.000 claims 1
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 96
239000000123 paper Substances 0.000 description 66
239000012948 isocyanate Substances 0.000 description 39
150000002513 isocyanates Chemical class 0.000 description 37
229920000570 polyether Polymers 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
239000004721 Polyphenylene oxide Substances 0.000 description 31
239000003795 chemical substances by application Substances 0.000 description 30
230000008569 process Effects 0.000 description 26
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 22
125000001165 hydrophobic group Chemical group 0.000 description 22
238000004513 sizing Methods 0.000 description 22
150000001412 amines Chemical class 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
229920000233 poly(alkylene oxides) Polymers 0.000 description 17
239000000047 product Substances 0.000 description 17
239000000839 emulsion Substances 0.000 description 15
229920003171 Poly (ethylene oxide) Polymers 0.000 description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
238000009833 condensation Methods 0.000 description 12
230000000694 effects Effects 0.000 description 12
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 12
125000002091 cationic group Chemical group 0.000 description 11
229920000962 poly(amidoamine) Polymers 0.000 description 11
125000004185 ester group Chemical group 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
125000002947 alkylene group Chemical group 0.000 description 8
239000002657 fibrous material Substances 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
229920000768 polyamine Polymers 0.000 description 8
239000000725 suspension Substances 0.000 description 8
KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 7
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
238000001035 drying Methods 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
230000009471 action Effects 0.000 description 6
125000003368 amide group Chemical group 0.000 description 6
230000005494 condensation Effects 0.000 description 6
239000000835 fiber Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000004814 polyurethane Substances 0.000 description 6
PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
239000000539 dimer Substances 0.000 description 5
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
229920002635 polyurethane Polymers 0.000 description 5
238000005956 quaternization reaction Methods 0.000 description 5
239000002994 raw material Substances 0.000 description 5
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000013543 active substance Substances 0.000 description 4
239000000654 additive Substances 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
229940100198 alkylating agent Drugs 0.000 description 4
239000002168 alkylating agent Substances 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000004945 emulsification Methods 0.000 description 4
239000011521 glass Substances 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229920000728 polyester Polymers 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
238000003756 stirring Methods 0.000 description 4
229910021653 sulphate ion Inorganic materials 0.000 description 4
239000013638 trimer Substances 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
230000014759 maintenance of location Effects 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000005588 protonation Effects 0.000 description 3
RQNOFUZGXHSHOT-UHFFFAOYSA-N 1-(diethylamino)ethanol Chemical compound CCN(CC)C(C)O RQNOFUZGXHSHOT-UHFFFAOYSA-N 0.000 description 2
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
JXHXARLTNDTXIZ-UHFFFAOYSA-N 5-isocyanatohexanoyl chloride Chemical compound O=C=NC(C)CCCC(Cl)=O JXHXARLTNDTXIZ-UHFFFAOYSA-N 0.000 description 2
235000018185 Betula X alpestris Nutrition 0.000 description 2
235000018212 Betula X uliginosa Nutrition 0.000 description 2
101000623895 Bos taurus Mucin-15 Proteins 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
235000011613 Pinus brutia Nutrition 0.000 description 2
241000018646 Pinus brutia Species 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000003750 conditioning effect Effects 0.000 description 2
238000011109 contamination Methods 0.000 description 2
229940008406 diethyl sulfate Drugs 0.000 description 2
125000004990 dihydroxyalkyl group Chemical group 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000011121 hardwood Substances 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920001451 polypropylene glycol Polymers 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
239000011122 softwood Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
229940014800 succinic anhydride Drugs 0.000 description 2
DCRQMOJXJXVZFC-UHFFFAOYSA-N trimethyl-[3-trimethylsilyloxy-2,2-bis(trimethylsilyloxymethyl)propoxy]silane Chemical compound C[Si](C)(C)OCC(CO[Si](C)(C)C)(CO[Si](C)(C)C)CO[Si](C)(C)C DCRQMOJXJXVZFC-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
NIXYMFJMHHIQAC-UHFFFAOYSA-N 1,1-bis(dimethylamino)propan-2-ol Chemical compound CC(O)C(N(C)C)N(C)C NIXYMFJMHHIQAC-UHFFFAOYSA-N 0.000 description 1
JGVZJRHAZOBPMW-UHFFFAOYSA-N 1,3-bis(dimethylamino)propan-2-ol Chemical compound CN(C)CC(O)CN(C)C JGVZJRHAZOBPMW-UHFFFAOYSA-N 0.000 description 1
SBNBXMDXLQOYRE-UHFFFAOYSA-N 1,3-bis[3-(dimethylamino)propoxy]propan-2-ol Chemical compound CN(C)CCCOCC(O)COCCCN(C)C SBNBXMDXLQOYRE-UHFFFAOYSA-N 0.000 description 1
OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
OUJCKESIGPLCRN-UHFFFAOYSA-N 1,5-diisocyanato-2,2-dimethylpentane Chemical compound O=C=NCC(C)(C)CCCN=C=O OUJCKESIGPLCRN-UHFFFAOYSA-N 0.000 description 1
QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 1
PVXVWWANJIWJOO-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-N-ethylpropan-2-amine Chemical compound CCNC(C)CC1=CC=C2OCOC2=C1 PVXVWWANJIWJOO-UHFFFAOYSA-N 0.000 description 1
MDLKWDQMIZRIBY-UHFFFAOYSA-N 1-(dimethylamino)ethanol Chemical compound CC(O)N(C)C MDLKWDQMIZRIBY-UHFFFAOYSA-N 0.000 description 1
SUZOCIFIGKCISE-UHFFFAOYSA-N 1-(dimethylamino)propan-1-ol Chemical compound CCC(O)N(C)C SUZOCIFIGKCISE-UHFFFAOYSA-N 0.000 description 1
FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
ISQUGNABFUCCEY-UHFFFAOYSA-N 1-[2-(diethylamino)ethoxy]-1-ethoxyethanol Chemical compound CCOC(C)(O)OCCN(CC)CC ISQUGNABFUCCEY-UHFFFAOYSA-N 0.000 description 1
SNCRCBCPLQSWSC-UHFFFAOYSA-N 1-[2-(diethylamino)ethoxy]ethanol Chemical compound CCN(CC)CCOC(C)O SNCRCBCPLQSWSC-UHFFFAOYSA-N 0.000 description 1
AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 description 1
RLAUGOOVNMKKCB-UHFFFAOYSA-N 1-isocyanato-4-(isocyanatomethyl)-1-methylcyclohexane Chemical compound O=C=NC1(C)CCC(CN=C=O)CC1 RLAUGOOVNMKKCB-UHFFFAOYSA-N 0.000 description 1
BAUWRHPMUVYFOD-UHFFFAOYSA-N 1-methylpiperidin-4-ol Chemical compound CN1CCC(O)CC1 BAUWRHPMUVYFOD-UHFFFAOYSA-N 0.000 description 1
GIEMHYCMBGELGY-UHFFFAOYSA-N 10-undecen-1-ol Chemical compound OCCCCCCCCCC=C GIEMHYCMBGELGY-UHFFFAOYSA-N 0.000 description 1
CJUFNCPPYUSJPR-UHFFFAOYSA-N 11-Hydroxystearic acid Chemical compound CCCCCCCC(O)CCCCCCCCCC(O)=O CJUFNCPPYUSJPR-UHFFFAOYSA-N 0.000 description 1
HXMBAEBQBJPOLX-UHFFFAOYSA-N 2,2-dichloropropane-1,1-diol Chemical compound ClC(C(O)O)(C)Cl HXMBAEBQBJPOLX-UHFFFAOYSA-N 0.000 description 1
SDMNEUXIWBRMPK-UHFFFAOYSA-N 2-(2-methylpiperazin-1-yl)ethanol Chemical compound CC1CNCCN1CCO SDMNEUXIWBRMPK-UHFFFAOYSA-N 0.000 description 1
KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical group CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 1
IEQWMHXOZQUIGJ-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-hydroxyethoxy)ethyl-methylamino]ethyl-methylamino]ethyl-methylamino]ethoxy]ethanol Chemical compound OCCOCCN(C)CCN(C)CCN(C)CCOCCO IEQWMHXOZQUIGJ-UHFFFAOYSA-N 0.000 description 1
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KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
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230000007613 environmental effect Effects 0.000 description 1
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150000004665 fatty acids Chemical group 0.000 description 1
239000012467 final product Substances 0.000 description 1
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150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
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230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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238000011065 in-situ storage Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
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DUDXQIXWPJMPRQ-UHFFFAOYSA-N isocyanatomethylcyclohexane Chemical compound O=C=NCC1CCCCC1 DUDXQIXWPJMPRQ-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
238000009533 lab test Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
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GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 description 1
239000003921 oil Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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235000021313 oleic acid Nutrition 0.000 description 1
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XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
150000002896 organic halogen compounds Chemical class 0.000 description 1
125000003544 oxime group Chemical group 0.000 description 1
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239000001301 oxygen Substances 0.000 description 1
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239000010893 paper waste Substances 0.000 description 1
239000011087 paperboard Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
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238000006068 polycondensation reaction Methods 0.000 description 1
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229920000582 polyisocyanurate Polymers 0.000 description 1
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229920000642 polymer Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
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230000008092 positive effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
229940116423 propylene glycol diacetate Drugs 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
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238000010008 shearing Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000003068 static effect Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
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150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000004381 surface treatment Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
238000005199 ultracentrifugation Methods 0.000 description 1
KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1
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239000000080 wetting agent Substances 0.000 description 1

Classifications

- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/07—Nitrogen-containing compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
- C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
- C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/07—Nitrogen-containing compounds
- D21H17/08—Isocyanates
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/53—Polyethers; Polyesters
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/18—Reinforcing agents
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/18—Reinforcing agents
- D21H21/20—Wet strength agents

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Dispersion Chemistry (AREA)
Polyurethanes Or Polyureas (AREA)
Paper (AREA)
Paints Or Removers (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

JP21359093A 1992-08-07 1993-08-06 紙仕上げ用の無塩素多官能樹脂 Expired - Fee Related JP3287660B2 (ja)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE4226110.4		1992-08-07
DE19924226110 DE4226110A1 (de)	1992-08-07	1992-08-07	Chlorfreie Naßfestmittel für Papier
DE4319571.7		1993-06-14
DE19934319571 DE4319571A1 (de)	1993-06-14	1993-06-14	Chlorfreie multifunktionelle Harze für die Papierveredlung

Publications (2)

Publication Number	Publication Date
JPH06173196A JPH06173196A (ja)	1994-06-21
JP3287660B2 true JP3287660B2 (ja)	2002-06-04

Family

ID=25917292

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP21359093A Expired - Fee Related JP3287660B2 (ja)	1992-08-07	1993-08-06	紙仕上げ用の無塩素多官能樹脂

Country Status (6)

Country	Link
US (2)	US5503714A (fr)
EP (1)	EP0582166B2 (fr)
JP (1)	JP3287660B2 (fr)
CA (1)	CA2101879A1 (fr)
DE (1)	DE59305310D1 (fr)
ES (1)	ES2098602T5 (fr)

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1993
- 1993-07-26 EP EP93111916A patent/EP0582166B2/fr not_active Expired - Lifetime
- 1993-07-26 ES ES93111916T patent/ES2098602T5/es not_active Expired - Lifetime
- 1993-07-26 DE DE59305310T patent/DE59305310D1/de not_active Expired - Fee Related
- 1993-07-30 US US08/100,024 patent/US5503714A/en not_active Expired - Fee Related
- 1993-08-04 CA CA002101879A patent/CA2101879A1/fr not_active Abandoned
- 1993-08-06 JP JP21359093A patent/JP3287660B2/ja not_active Expired - Fee Related
1995
- 1995-08-08 US US08/512,612 patent/US5739249A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0582166A1 (fr)	1994-02-09
EP0582166B1 (fr)	1997-01-29
US5739249A (en)	1998-04-14
CA2101879A1 (fr)	1994-02-08
DE59305310D1 (de)	1997-03-13
ES2098602T3 (es)	1997-05-01
EP0582166B2 (fr)	2000-08-23
JPH06173196A (ja)	1994-06-21
US5503714A (en)	1996-04-02
ES2098602T5 (es)	2000-12-01

Legal Events

Date	Code	Title	Description
2005-03-15	LAPS	Cancellation because of no payment of annual fees

Publication	Publication Date	Title
US5503714A (en)	1996-04-02	Chlorine-free multifunctional resins for paper finishing
US4670100A (en)	1987-06-02	Aqueous solutions or dispersions of polyisocyanate addition products, a process for their preparation, and their use as coating compounds or as sizing agents for paper
US6090871A (en)	2000-07-18	Paper finishing aid
US9551110B2 (en)	2017-01-24	Fluorochemical composition and use thereof
JP3274736B2 (ja)	2002-04-15	紙に湿潤強度を賦与するための方法
US3971764A (en)	1976-07-27	Process for producing a cationic polyurethane
US5718804A (en)	1998-02-17	Process for the production of cellulose-containing sheet-like structures which have been given a dry strength and/or wet strength treatment
FI81859B (fi)	1990-08-31	Polyuretanlatex, som kan anvaendas som limaemne i pappersindustrin, och foerfarande foer framstaellning av detta.
US6201060B1 (en)	2001-03-13	Water dispersable, isocyanates with enhanced absorbing capacity as paper auxiliary agents
DE4419572A1 (de)	1995-11-16	Mehrkomponenten-Systeme für die Papierveredelung
US6080831A (en)	2000-06-27	Water-dispersible polyisocyanates
US4786330A (en)	1988-11-22	Diurethane latex and processes
AU701726B2 (en)	1999-02-04	Process for the production of structurally strong papers
EP0986673A1 (fr)	2000-03-22	Isocyanate auto-emulsifiable et compositions d'agents de couplage permettant d'ameliorer la resistance et les proprietes collantes de fibres cellulosiques, et son procede de fabrication et d'utilisation
DE4226110A1 (de)	1994-02-10	Chlorfreie Naßfestmittel für Papier
DE4319571A1 (de)	1994-12-15	Chlorfreie multifunktionelle Harze für die Papierveredlung
JP2002505358A (ja)	2002-02-19	再パルプ化可能な紙を製造するための水分散性ポリイソシアナート製剤